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Exchange 2007 - proxyAddresses and external mail server.

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Hi all,

I've got an issue with Exchange 2007 and an Exchange Online mail service (Office365). I was pointed here for additional assistance. The issue is Exchange 2007 users cannot mail Office365 users. I have verified it's not on the Office365 end as I can send and receive emails from other services such as Google Mail.

Background:

We have 3 domains, I'll name them as colors to distinguish them and for privacy reasons. Here's the list with their purpose:

  • white.local.lan - internal domain
  • red.com - Faculty Email Domain (Exchange 2007) and Website Domain
  • blue.com - Students Email Domain (Exchange Online via Office365)

We have created a UPN suffix of blue.com in order to match them with the Office365 domain. All students are assigned this suffix. We have created records in the proxyAddresses attribute of Active Directory for the purpose of DirSync via Forefront Identity Manager. This is working well.

Every time we send an email to an address in the proxyAddresses attribute we get bounce messages as follows:

Delivery has failed to these recipients or distribution lists:

John Smith
The recipient's e-mail address was not found in the recipient's e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the e-mail address and try resending this message, or provide the following diagnostic text to your system administrator. _____ Sent by Microsoft Exchange Server 2007 Diagnostic information for administrators: Generating server: EXCHANGE.white.local.lan IMCEAEX-_O=NT5_ou=3865e760e8c9484fafde58fe9e1f40cf_cn=9e9257a09938de4ca69181ebb94aff38@red.com #550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ## Original message headers: Received: from EXCHANGE.white.local.lan  ([...]) by EXCHANGE.white.local.lan  ([...]) with mapi; Thu, 22 Aug 2013 16:11:09 +1000 Content-Type: application/ms-tnef; name="winmail.dat" Content-Transfer-Encoding: binary From: James Elliott <James.Elliott@red.com> To: John Smith    <IMCEAEX-_O=NT5_ou=3865e760e8c9484fafde58fe9e1f40cf_cn=9e9257a09938de4ca69181ebb94aff38@red.com> Date: Thu, 22 Aug 2013 16:10:51 +1000 Subject: Outbound Test
Thread-Topic: Outbound Test Thread-Index: Ac6e/lgzDPoWcQUgSC6bvsDNW0O2dg== Message-ID: <ADBD636EDF962E4AB0F6B86D7399B14301D1274D4B@EXCHANGE.white.local.lan> Accept-Language: en-US, en-AU Content-Language: en-US X-MS-Has-Attach: yes X-MS-TNEF-Correlator: <ADBD636EDF962E4AB0F6B86D7399B14301D1274D4B@EXCHANGE.white.local.lan> MIME-Version: 1.0

Destination User Attributes (UPN: smithj@blue.com):

proxyAddresses:

SMTP:John.Smith@blue.com;smtp:smithj@blue.com;SIP:John.Smith@blue.com


mail:

John.Smith@blue.com

mailNickname

<not set>

We have set up the following in Exchange 2007:

[Organization Configuration] -> [Accepted Domains]

Accepted Domain: blue.com
Default: False
After MSEXCH Accepts: External Relay Domain

[Organization Configuration] -> [Send Connectors]

GENERAL
Protocol Logging Level: None
Specify the FQDN this connector will provide in response to HELO or EHLO:<blank>
Max Message Size (KB): 10240

ADDRESS SPACE
Type: SMTP
Address: blue.com
Cost: 1
Scoped Send Connector: unchecked / no

NETWORK
Select how to send mail with this connector: Use domain name system (DNS) "MX" records to route mail automatically
Enable Domain Security (Mutual Auth TLS): unchecked / no
Use the External DNS Lookup Settings on the transport server: checked / yes

SOURCE SERVER
Name:<Exchange Hostname>
Site: <Site Name>
Role: Mailbox, Client Access, Hub Transport





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